Bothsides Podcast25 Aug 2025

EP 127 | Simon Caulfield: Player–Coach Leadership & Legacy

In this episode, Director of Place Kangaroo Point, Simon Caulfield unpacks how he’s built an office where top performers have their own identities—not “from Simon’s office”—and why the business must thrive without him.

We get into pathways from 500k GCI to seven figures, case studies across high-volume vs high-value models, and Simon’s personal playbook: two champagne COI events a year, a “favorites” list he calls religiously, and being a present, trusted local over flashy ads.

In this Simon shares lessons from moving upmarket (from $555k beginnings to KP’s top end), the difference between selling resi and selling the dream off-the-plan, and the player-coach balance of leading six team presentations a week while still listing and selling.

He dives into Wolfpack Fridays, retaining top talent by giving them reasons to stay, using an AI recorder to capture meetings and train staff, and the three-corner support team (manager, coach, trainer). Above all: listen intently, play to your strengths, move the needle each year, and leave people in a better place than you found them.

Topics covered:

Building a business where agents thrive under their own brands
Leadership mindset: “Leave people in a better place”
Pathways from 500k to $1M+ GCI and choosing the right model
Case studies: high-value vs high-volume strategies
Simon’s COI playbook: champagne events & “diamond” call list
Moving upmarket: perception, results, and social proof
Resi vs off-the-plan: selling the dream before it exists
Player–coach leadership and when to step back from listing
Wolfpack Fridays: training, collaboration, and shared challenges
Retaining top talent with support, recognition, and care
Practical AI for onboarding and process improvement

Legacy: success measured by impact, not trophies

You can watch us on ⁠Youtube ⁠

Find us on ⁠Instagram⁠

Join us on ⁠Tik Tok ⁠

Visit us on ⁠Website⁠

Thank you so much for listening!

Denne episoden er hentet fra en åpen RSS-feed og er ikke publisert av Podme. Den kan derfor inneholde annonser.

Episoder(155)

10 Lessons From Interviewing 8 & 9-Figure Founders

Marty Fox. Jack Delosa. Graeme Holm. Jack Henderson. Marcus Chiminello. Gavin Rubinstein. Sam Gordon.Over 150 episodes with some of the best in Australian property and business, and ten lessons that c...

31 Aug 31min

Teal: How To Master Your Mind, Know Your Worth & Become Successful - #153

Why do the most successful people seem to operate on something other than logic alone? Psychic Teal breaks down how she believes the mind can actually be rewired — through psilocybin, breath work, and...

25 Aug 1h 43min

Property Masterclass: The Most Valuable 90 Minutes For Any Buyer in 2026 - No BS Property Show #2

The part most buyers never figure out: it's not about finding the perfect property, it's about reading your own position on the grid before you even start looking.In this episode, we sit down with Mat...

17 Aug 1h 36min

Commando Steve: What The Army Taught Me About Winning At Life - #152

Steve Willis, known to most of Australia as "Commando Steve," spent over a decade in the Australian Special Forces, rising to Counter Terrorism Team Commander before leaving the army in 2004.He went o...

10 Aug 2h 7min

It's time to share my story...

In this episode, I turn the mic on myself...Issy sits down with me to unpack where my drive really comes from, starting with the day everything changed.I was 7 years old, standing at the end of a hosp...

3 Aug 52min

Why Australia Is Making It Harder To Get Rich - Jack Henderson #151

Australia's property market is at a breaking point, and the people who built their fortunes in it are already responding.In this episode, Jack Henderson, one of Australia's most talked-about buyer's a...

27 Jul 1h 20min

Is Now The Best Time To Buy Property In Australia? - No BS Property Show #1

Welcome to the No BS Property Show, a series within Bothsides, where we sit down to talk property, investing, and everything you need to actually succeed in the Australian market... straight up, no fi...

20 Jul 56min

EP 150| Emil Juresic: "The Market Has Already Dropped 10 To 30%" And More Pain Is Coming

Emil Juresic sold every property he owned five months before Australia's housing market turned. Now he's revealing the exact prediction that got him out at the peak, why he believes there's more pain ...

13 Jul 1h 6min